Mommy(ies) and Son Date Night: Arrow Edition
by changingdestiny40
Summary: Oliver is unable to have his monthly night out with his wives Sara and Nyssa, so he has his son fill in for him. Assassin Canarrow
1. Chapter 1

**Hello everyone. This fic will be an "Arrow" version of my other "Star Wars" fic entitled "Mommy and Son Date Night, which was inspired by Jedi Jesi Jiin entitled "Blind Date".**

 **Disclaimer: I don't own "Arrow" or its characters. They're the property of DC, Warner Brothers, the CW, and its showrunners.**

"Are you sure we can't go out tonight on our monthly date night Oli?", asked Sara with great disappointment while Nyssa, standing next to them, was also feeling quite despondent. Every month, Oliver and his wives Sara and Nyssa selected an evening out of each month to have a romantic dinner together, a date night as mentioned above. But to the consternation of all three, Oliver had been called to the office in order to finalize the merger between his company, Queen Incorporated, and Wayne Technologies, the company owned by Mr. Wayne, a famous but mysterious billionaire from Gotham. And this merger was very important for Oliver's company and the board was putting tremendous pressure on him to see this through.

"I really wish we could, but the board is absolutely insistent that this merger between mine and Mr. Wayne's company is settled quickly and they won't take no for an answer in regards to getting it done tonight. I'm upset about it as much as you guys are, but my hands are practically tied. Don't worry though, I promise to make it up to you tomorrow evening, and I'm truly sorry about this."

Nyssa huffed in annoyance at this but believed her husband's words that he would make things up with her and Sara. Sara on her part also believed him but that didn't make her any less frustrated by this dreadful situation.

"You should really call up your board members and gives them a piece of your mind. In fact, you should tell them that they either let you finalize the deal another evening or you'll use each of them as target practice for your arrows", said Nyssa as her aggravation continued to grow. In fact, that's exactly what she wanted to do if she were the CEO.

"You know I can't do that honey, though I admit that it is tempting and something that crossed my mind", replied Oliver with amusement to his wife's words while totally understanding where she was coming from. Suddenly, a brilliant idea flashed above Oliver's head, and as he began to reflect on it, he was more convinced that it was indeed a brilliant idea and voiced it to his wives.

"You know what, you my loves deserve a nice evening out and I have a wonderful idea as to how it can be accomplished. What if the two of you were to go out and enjoy a nice evening, but with Connor as your escort in my stead?" Connor was the 11 year old son of Oliver and Sara, but was also every bit Nyssa's son as much as Oliver's and Sara's.

Hearing Oliver's suggestion brought surprised looks upon Sara and Nyssa's faces. They hadn't even thought of that arrangement. But now that he mentioned it, it actually sounded indeed like a suitable plan.

"I actually like that idea very much Oli", responded Sara in agreement with her husband's suggestion, really pleased with the idea. "Even though the three of us can't have our usual romantic evening out, me and Nyssa having a nice mothers and son evening with Connor is a great alternative. And I really could enjoy having a nice dinner out tonight."

"I also second it as well my love", added Nyssa, liking it as much as Sara and Oliver did.

"Then it's settled. You ladies go ahead and get dressed while I go and talk to Connor". Oliver then went ahead to do exactly that while Sara and Nyssa headed to their room to get themselves ready for the night.

ARROW

Connor was sitting in his room upstairs reading _"Michael Vey: Rise Of The Elgen"_ when there was a knock at his door. After placing his book aside, he opened the door and saw his father standing on the other side.

"Hey buddy, how're you doing?"

"I'm doing okay dad, just reading my book which is really awesome."

"I'm not surprised, it's actually a very good series. However, the reason I'm here is to ask a really big favor of you."

"What is it dad", Connor asked, curious as to what his dad wanted.

"I had planned to take your moms out to dinner tonight as part of our monthly date night, but there's something I have to take care of at work and won't be able to do so. But I'm wondering if you'd be willing to accompany your mothers in my place please. It would mean a lot to me and them."

Connor was very surprised after hearing his dad's request, but he could see how important this was to him and didn't want to let him down. He also knew how important this was to his moms since having a nice evening out meant a lot to them. And he was a very good boy who helped his parents whenever they needed it and really wanted them to be happy. With those thoughts in mind, he gave his answer.

"Sure dad, I'll do it, but there's something I'd really like to do please."

"What might that be?", Oliver asked his son curiously.

"I'd like to use my allowance in my wallet to pay for dinner please. After all, since you want me to take my moms out, I think I should pay just like you do when you guys go out. And you did say that I could use my allowance or anything as long as I'm responsible, and I think doing the paying is responsible. Please let me do it dad", begged Connor, very eager to follow his father's example.

Oliver on his part was also surprised at what his son wanted to do, but impressed.

"Sure go right ahead son. Now please hurry up and get ready. You shouldn't keep your moms waiting. In fact, it's never a good idea to keep a lady waiting."

"Okay dad", replied Connor after which he went to his closet and quickly got dressed while Oliver had moved outside his son's room in order to wait for him. Four minutes later, Connor stepped out of his closet wearing a nice clean pair of black trousers, a long white sleeved shirt, and a dark green jacket. He also made sure to get his wallet and then stepped out of his bedroom to where his dad was, who expressed his approval of his son's choice in attire. Afterwards they made their way downstairs to where Sara and Nyssa were waiting, having finished getting dressed. Sara wore a beautiful golden colored sleeveless dress and a pearl necklace around her neck while her hair was styled into a ponytail that hung across her shoulder. Nyssa on her part wore a beautiful red gown with shoulder straps while her own hair was curled into ringlets and a pearl necklace around her own neck.

"Wow, you guys look very pretty", said Connor with his mouth slightly opened in awe of his moms appearance.

"Why thank you dear, that's a very sweet thing to say about us", responded Sara to her son's kind words.

"She's right honey, that was a lovely thing to say, and I'm glad you approve", added Nyssa with a smile directed towards Connor. Everyone then checked to make sure they had what they needed while Oliver asked Connor to take good care of his moms for him while they were out. Being satisfied that everything was in order, made their way out the door with Oliver headed to his limo which would take him to the office where his impatient board was waiting while Sara, Nyssa, and Connor headed to the limo that would take them to their chosen restaurant.


	2. Chapter 2

**Disclaimer: I don't own "Arrow"**

Sara, Nyssa, and Connor arrived at the restaurant, which was _Pappasitos,_ went inside, and after giving their names to the maître d', were led by him to a nice booth in which they were seated. Afterwards, they ordered their drinks which the waiter provided, two glasses of wine for Sara and Nyssa and a glass of sparkling grape juice for Connor. They then looked through the menu before deciding on what they wanted. Connor ordered the chicken enchiladas with rice and whole beans, a meal which he really enjoyed, while Sara and Nyssa ordered steak fajitas with guacamole and whole beans on the side. As they waited for their dinners to arrive, they conversed among themselves regarding what they did that day.

"Today at school, I learned about the Persians trying to conquer the Greeks but the Greeks managed to stop them instead. I also found out that the Persian King built some kind of bridges to cross some lakes, but a storm came through which destroyed those bridges. The king was so angry that he threw large chains into the lakes and had them whipped in order to show them that he was their master. Pretty silly right?"

"You're right honey", replied Sara to what her son told her with amusement in her tone. Though for the life of her, she couldn't remember that particular part in her history lessons when she learned about the Persians attempted conquest of the Greeks. Nyssa on her part just shook her head with a smile, pondering as to how foolish and arrogant men could be, especially kings.

"I also drew some pictures today of us and dad's time together at the zoo after coming home from school, and then I played with my ' _Halo_ ' video game until you guys and dad returned home", continued Connor as he happily told his moms about his day. Sara and Nyssa on their part also shared with Connor some of what they did that afternoon.

"While you were at school, your mother and myself went to the mall in order to purchase some new dishes for our home, and we also visited your Aunt Thea and Uncle Roy at their home", said Nyssa while describing her and Sara's day to their son.

How are Auntie Thea and Uncle Roy doing?", Connor asked eagerly, really wanting to know how his aunt and uncle were. They were literally his favorite uncle and aunt and were a lot of fun to hang out with.

"They're doing well and miss you very much. In fact, they asked us to tell you hello for them and plan on visiting soon", Sara answered to Connor's inquiry, her answer making him very excited and giving him something to look forward to. The waiter then arrived with everyone's food and set them onto the table after which Sara, Nyssa, and Connor began to dig in to their dinners, enjoying them immensely. As they ate, they continued to talk about different subjects that interested them both while genuinely interested in hearing what each other had to say.

One subject Sara and Nyssa didn't discuss with Connor was their vigilante work. He already knew about what his moms, dad, and his aunt and uncle did for the city, but he had agreed with all of them not to talk about that particular subject when out in public.

Eventually they finished their dinners and afterwards the waiter took their plates then brought them the bill. As Sara and Nyssa were about to get the money from their purse to pay it, Connor quickly took out his wallet and to his moms astonishment, took some of his money from it and paid for the bill himself. The waiter himself was quite astounded himself since this wasn't something he usually saw, but he quickly composed himself and gave the boy an impressed smile while taking the bill away and then wished him and his moms a very good night.

Afterwards, the three of them left the limo and began making their way to _Marble Slab_ for dessert. As they headed there, Sara asked her son the question that was in both her and Nyssa's minds.

"What on earth caused you to use your own money to pay for the bill instead of letting me and your other mom pay it?"

"Well mom, I asked dad if I could use some of the money from my allowance to pay for it and he said yes. I know that dad is the one who pays for it after you guys have dinner, and since he had me take his place tonight, I figured that I should also pay the bill like he did. Are you mad?" Connor asked with a worried look on his face.

Once they heard Connor's explanation, Sara and Nyssa were moved to tears at their son's generosity and quickly hugged him close to them.

"Of course we're not mad dear", answered Nyssa while she and Sara reassured their son that he wasn't in trouble. "We were just surprised by your actions. What you did was actually a very kind gesture and showed real maturity for your age _ **."**_

"Thank you very much mommy, and I'm glad you and mom liked it", answered Connor, very happy with having his moms approval. They then arrived at _Marble Slab_ Sara and Nyssa each got a Fudge Brownie delight for themselves while Connor got an Apple Pie A La Mode for himself. They then took seats inside of the ice cream parlor and contentedly ate their desserts while sharing them with each other. After finishing, they returned to their limo and began the drive back home, thoroughly happy with how the evening had turned out.


	3. Chapter 3

**Disclaimer: I don't own "Arrow"**

Having arrived back at their home, Sara, Nyssa, and Connor climbed out of their limo, closed the door, and after Connor tucked his arms under his mothers arms like a gentleman, they made their way to the front door. Once there, both Sara and Nyssa stooped down so that they were at eye level with their son and each of them placed a hand on each shoulder.

"Thank you so much for filling in for your father tonight", Nyssa said to him while giving him a warm smile.

"Yes Connor, we really appreciated what you did and had a great time with you this evening. You've made the two up of us very happy", added Sara while also giving him a big smile.

"Thank you very much mom and mommy, and I'm glad you enjoyed everything", replied the boy with a bright smile on his own face. At that moment, Nyssa thought of something interesting and quickly whispered it in Sara's ear. Taking a very brief moment to think on what Nyssa told her, Sara decided that it was a nice idea on how to conclude the evening and that their son deserved it, but only for tonight, which Nyssa agreed to. They then turned their attention back to their son.

"We've just been thinking honey, and have decided that since you've done such a good job taking your father's place in accompanying us, were a perfect gentleman, went as far as to pay the dinner bill, and this evening was similar to a date, we believe you deserve a proper goodnight kiss", Sara told Connor, both her and Nyssa having mischievous twinkles in their eyes. Sara then wrapped her arms around her son, pressed her lips to his, and gave him a big semi long kiss. After they parted, Nyssa also took Connor in her arms and planted a big kiss on his lips as well. Connor was quite surprised by this turn of events but definitely enjoyed it.

"You must understand however, that this was only a onetime thing for tonight", Nyssa said seriously but kindly.

"She's right honey", added Sara, also seriously but kindly. "We just wanted to give you a special treat for the reasons we mentioned earlier. But our lips will ultimately belong to your father's."

"I understand, and thank you guys for giving me my first kiss", replied Connor.

"You're very welcome dear", Sara answered her son, her and Nyssa smiling at his words. The three of them then entered their home, and Connor went back upstairs to his bedroom and went to bed after bidding his moms goodnight while they entered their own bedroom upstairs which they shared with Oliver and changed from their gowns to their nighties. Afterwards, they got underneath their bed covers and waited for Oliver to return home. He returned ten minutes later, the merger between his company and Wayne Technologies complete, and headed upstairs to his wives.

"Did the two of you enjoy your evening with our son, and did he take good care of you and was he on his best behavior?", he asked after greeting them, eager to know how things went.

"We did very much", answered Nyssa. "And he was a perfect gentleman who did an excellent job acting as our escort. We were surprised when he paid the dinner bill and he told us that he spoke to you first regarding that subject. We did appreciate it though and told him that was a very mature action for him to do."

"I myself was surprised by Connor wanting to do that, but was also very proud of him."

"So were we Oli", replied Sara. "And because of that along with his doing such a good job filling in for you, me and Nyssa gave him his first kiss as a thank you. We did tell him that it would only be a one time thing however."

"In that case, I'm glad it was you guys who gave Connor his first kiss instead of some girl at school who we don't even know", responded Oliver with amusement in his voice, a statement to which his wives agreed with whole heartedly. They then took ahold of his arms and dragged him into the bed with them while smiling at him seductively.

"Now that you're home Oli, and we've had our quality time with our son who's most likely asleep by now, I believe it's now time for us to have some quality time with our shared husband. What do you think Nyssa?"

"Oh most definitely Sara, it's past time and why should we wait until tomorrow for a nice evening with our husband? Therefore, I command you Oliver Jonas Queen to immediately make love to your lovely wives and show us the prowess we so love about you."

"You know I can never refuse either of you, and as always, your wishes are indeed my commands", said Oliver who then got under the covers with Sara and Nyssa to do exactly that, the three of them making passionate love for most of the night and enjoying every minute of it.

 **The End**

 **A/N I don't own if there are any** _ **Pappasitos**_ **or** _ **Marble Slabs**_ **in the east coast, where I assume the Arrow/Flash universe is located, but because the food at that restaurant is absolutely delicious and the ice cream is always a treat to enjoy, I chose those places to serve as Connor and his moms dinner and dessert. I also had Connor order the chicken enchiladas and the apple pie a la mode because those are my favorite foods over there. But for some reason,** _ **Marble Slab**_ **doesn't seem to be carrying apple pie a la mode anymore. That's a shame. Also, that information about the Persian King who whipped and then placed chains into the lakes is a true historical account, no joke. That shows how stupid some people can be.**

 **The reason I've written this fic along with my other Assassin Canarrow (Nyssa/Oliver/Sara) and Canarrow (Oliver/Sara) fics is because even though I ship Olicity, I also ship Oliver/Sara and want to draw attention to them in addition to wanting to see what an Oliver/Nyssa romance on canon would be like. And there's more than enough Olicity on this site (over 1,000). Therefore, my goal is to fill up this site with Assassin Canarrow and Canarrow stories. So far, a few authors have agreed to join me and I would like to invite others to join us as well. One of my ultimate goals is to reach 1,000 since that's over how many Olicity stories there are, but I can't do that without the help of any of you who like the Canarrow and Assassin Canarrow pairings. I also want to create a new large and popular fandom for Oliver/Sara and Nyssa/Oliver/Sara that will hopefully serve as the backup pairing in order to show the "Arrow" showrunners which pairing we'd prefer to replace Olicity if it ends on canon. And I really don't want Oliver to be with Laurel. Therefore, if anyone here ships Oliver/Sara, Oliver/Nyssa, likes multi pairings, feels there's more than enough Olicity, BUT AT THE SAME TIME, does NOT want Oliver to be with Laurel, and wants either Oliver/Sara or Nyssa/Oliver/Sara to be endgame on canon if Olicity ends, please join me in my mission to fill up this site with a multitude of Assassin Canarrow and Canarrow stories. I REALLY need the help of as many of you as possible and your support would be most appreciated. And your stories can be any length you're comfortable writing. But please consider marking your stories as Nyssa/Oliver/Sara and Oliver/Sara in order to make clear to readers what types of stories they are. I've personally chosen to do the same.**

 **If anyone here wants to write a prequel or sequel to this fic, please do. You have my permission and encouragement to do so.**

 **Here's a new story idea or challenge for anyone who wants to accept. After Oliver and Sara's showdown with Slade at the end of the season 2 flashbacks, there's both found and taken into the League by Nyssa, after which Oliver, Sara, and Nyssa end up in a threeway romantic relationship. I have some other story ideas or challenges at the end of my other Assassin Canarrow and Canarrow stories for you all to use except for the ideas in "Arrow and Canary Wedding", "The First Date", and "Nanda Parbat Wedding". Those particular ideas are taken.**

 **Merry Christmas everyone.**


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